Treatment of textile fabrics with methylglycidyl ethers



United States Patent race 3,025,215 Patented Mar. 20, 1962 3,926,216TREATP/ENI F TEXTILE FABRICS WiTH METHYLGLYKITDYL ETHERS Arnold M.Scoltne, Silver Spring, Md., and Howard R. Guest, Charieston, and Joe T.Adams, St. Albans, W. Va, assignors to Union Carbide Corporation, acorporation of New York No Drawing. Fiied Oct. 5, 1959, Ser. No. 844,17112 Claims. (Cl. 1171? 9.4)

This invention relates, in general, to a process for the treatment ofcellulosic textile materials. In one aspect, this invention relates tothe treatment of cellulosic and cellulosic-containing textile fabricswith methyiglycidyl ethers.

This application is a continuation-in-part of application Serial No.833,688, filed August 14, 1959, by H. R. Guest, J. T. Adams and A. M.Sookne, entitled Stabilized Textile Treating Solutions and Process forTheir Use, and assigned to the same assignee as the instant invention.

With the increased use of synthetic fibers, textile materials have beenproduced which can be washed, dried and worn with little or no ironing.These wash-andwear properties of the synthetic fibers have stimulated acorresponding technological advancement in the field of the cellulosicfibers so that today, crease and shrink resistant properties can beimparted to cotton, rayon and linen fabrics by the use of appropriatechemical finishes. The most commonly used finishes are the formaldehydereaction products of nitrogen-containing chemicals such asureaformaldehyde, melamine-formaldehyde, dimethylol ethylene urea andthe like. While the treatment of cellulosic fabrics with theaforementioned finishes imparts to the fabric the desired shape-holdingproperties, the use of nitrogen-containing finishes is subject toseveral disadvantages. For example, the effectiveness of thesetreatments diminishes after repeated commercial launderings and suchfinishes tend to retain chlorine from bleaching solutions which resultsboth in a yellowing of the fabric and a measurable loss of strengthafter ironing.

The more recent developments of new finishes have been directed to thepolyepoxides which can be applied to the textile fabric in the form ofan aqueous emulsion or dissolved in a solvent miscible with water andthen cured within the fibers by means of an epoxy curing agent. Sincethe polyepoxides usually contain no nitrogen, they are of particularinterest for they do not exhibit the chlorine retentive characteristicsof the earlier chemical finishes. Several polyepoxides, particularly thepolymers of the glycidyl ethers of aliphatic alcohols or polyols havebeen utilized either alone or in combination with polyaldehydes,polymethylol-substituted phenolic compounds and other components to givecrease and shrink resistant properties to textile materials. Thepolyepoxides, while an improvement in many respects over thenitrogen-containing finishes are still subject to certain deficiencies.The use of a softener is required in many cases to overcome the harshfeel of the fabric imparted by the polyepoxide finish while theyellowing of the softener itself during curing may necessitate the useof a bleach. While a few of the polyepoxides are slightly soluble inwater, their solubility is such that it is not advantageous to preparetreating baths of such low concentrations since it would necessitaterepeated padding to obtain the desired add-on of polyepoxide. For thisreason, the polyepoxide usually requires an emulsifying agent ornon-aqueous solvent to prepare a bath of suitable concentration. This isparticularly true when the polymers or copolymers of theepoxy-containing monomers, or monomers of high molecular weight areused. Additionally, when used in combination with other components, thesolubility can be even less. In many instances, the presence of anemulsifying agent makes the curing of the polyepoxide more difificult tocatalyze and even yellows the fabric to a greater degree than do thenitrogen-containing finishes. The use of non-aqueous solvents tocircumvent the low Water solubility of the polyepoxide finishes alsocreates plant operating problems which detract from their otheradvantages.

A further disadvantage which has also been observed is that many of thepolyepoxides tend to undergo hydrolysis with water with the net resultthat the amount of the polyepoxide in the treating solution availablefor cross-linking decreases as the hydrolysis reaction proceeds. Due tothe acidic nature of many of the catalytic agents employed, thisoccurrence is greatly aggravated where the epoxy-curing agent is presentin the treating solution. It has been observed that textile treatingsolutions containing polyepoxides and having hydrogen ion concentrationswithin the range of a pH value of from about 5.5 to 7.5 are fairlystable with relatively little hydrolysis, while, on the other hand, at apH of approximately 3, or lower, the polyepoxide undergoes rather rapidhydrolysis with the net result that there are fewer epoxy groundsavailable for reaction with the cellulosic fabirc.

Accordingly, one or more of the following objects will be achieved bythe practice of the instant invention. It is an object of the presentinvention to provide a process for the treatment of cellulosic andcellulosic-containing textile materials wherein the disadvantagespreviously indicated are substantially eliminated. It is also an objectof the present invention to provide a process for impregnatingcellulosic textile materials with monomeric polyepoxide compoundswhereby the materials are rendered both shrink and crease resistant,while imparting to the material after laundering, a soft, smooth finishwithout ironing. It is a further object to provide a process fortreating textile fabrics which will not exhibit un desirable chlorineretention properties and which are durable to laundering. Another objectof the present invention is to provide a process for treating textilematerials which does not require the used of emulsifying agents ornon-aqueous solvents. A further object is to provide textile treatingsolutions containing polyepoxides which when applied to a textile fabriccan be cured quickly and at temperatures lower than heretofore possible.A still further object of the present invention is to provide textiletreating solutions containing polyepoxides which are stable for extendedperiods of time. These and other objects will readily become apparent tothose skilled in the art in the light of the teachings herein set forth.

A broad aspect of this invention is directed to a process for treatingcellulosic and cellulosic-containing textile materials with a textiletreating solution containing one or more polyepoxides whereby a softsmooth finish is imparted to the fabric after laundering without theneed for ironing. Specifically, this aspect of the present invention isdirected to a process for treating cellulosic and cellulosic-containingtextile materials whereby the material is rendered both shrink andcrease resistant while imparting to the material after laundering asoft, smooth finish without ironing which comprises impregnating thetextile material with a textile treating solution comprising a monomericpolyepoxide having at least one CH2CCHr-O group, an epoxy curingcatalyst and then heating the textile material to cure the polyepoxide.

The polyepoxide compounds employed in the practice of this invention arepreferably aliphatic and free of el e 3. merits other than carbon,hydrogen and oxygen. Preferred compounds are thebis(2,3-epoxy-2-methylpropyl) ethers of glycols. Particularly preferredcompounds are those containing from 8 to 14 carbons atoms. Examples ofthe polyepoxides include, among others, the methylglycidyl ethers suchas bis(2,3-epoxy-2-m'ethylpropyl)- ether, ethylene glycolbis(2,3-epoxy-2-methylpropyl) ether, diethylene glycolbis(2,3-epoxy-2-methylpropyl)ether, propylene glycolbis(2,3-epoXy-2-methylpropyl)ether, trimethylene glycolbis(2,3-epoxy-2-methylpropyl)ether, 1,4- butanediolbis(2,3-epoxy-2-methylpropyl)ether, 1,3-butanediolbis(2,3-epoxy-2-rnethylpropyl)ether, 2,3-butanediolbis(2,3-epoxy-2-methylpropyl)ether, 1,5-pentanediolbis(2,3-epoxy-2-methylpropyl)ether, 1,6-hexanediol bis-2,3-epoxy-2-methylpropyl) ether, and the like.

The preparation of ethylene glycol bis( 2,3-epoXy-2- methylpropyl)etherand diethylene glycol bis(2,3-epoxy-2- methylpropyl)ether is disclosedin a copending application entitled Methylglycidyl Ethers, filed thesame day as the present invention by B. Phillips and F. C. Frostick, Jr.7

Although other methylglycidyl ethers are equally adaptable for use inthe process of this invention, it should be noted that the abovecompounds are monomeric polyepoxides in contrast to the water-insolublepolymeric-type polyepoxides heretofore known. The polymeric polyepoxidespossess many of the disadvantages previously indicated, particularly thenecessity for using volatile solvents or aqueous emulsions to preparethe treating bath. The methyl-substituted glycidyl ethers are preferredover the unsubstituted glycidyl ethers in that they can be cured quicklyand at temperatures lower than heretofore possible. The polyepoxidecompounds employed herein can be cured on the fabric at a temperature of120 C. in contrast to temperatures of from 130 C. to 190 C. recommendedfor the unsubstituted glycidyl polyethers. A low curing temperature is adecided advantage in cornmercial cotton finishing since it results inless damaging effect on the color and the fabric itself. At the highertemperatures fabrics treated with polyepoxides have been known to sufierdegradation and strength loss from the action of the epoxy curingcatalyst. Fabrics treated with methylglycidyl ethers by the process ofthis invention therefore show a lower strength loss at a particularlevel of crease recovery than do other commercial polyepoxides.

The term cellulosic and cellulosic-containing textile materials as usedthroughout the specification and claims is intended to include celluloseor cellulose-containing fibers, whether in the finished state or at someintermediate stage in processing; cellulose and cellulose-containingfabrics whether wovenor knitted; and garments or other articles madefrom such fabrics. Thus, materials containing cellulose, regeneratedcellulose, and mixtures of the two are intended to be within the scopeof the present invention.

By applying the polyepoXides of this invention in the form of a stableaqueous solution, the disadvantages inherent in the past have beenovercome to give a fabric which is soft, white and has a high degree ofcrease recovery, shrink resistance and Wash-and -wear characteristics.The cellulosic textile fabrics treated by the process of this inventionretain these properties well after repeated laundering and arenot'subjected to chlorine retention. Both whiteness and the originalstrength of the fabric are retained to a surprisingly high degree.Treatment by the method of this invention represents an improvement overother highly durable, non-chlorine retentive finishes heretoforeavailable.

While the polyepoxide finishes generally in use are not easily dispersedin a treating bath to give a homogeneous solution because of thepresence of water insoluble polymers, the methylglycidyl ethers employedin the process of this invention have a distinct advantage of having ahigh solubility in water so that solvents or emulsifying agents are notnecessary in preparing the treating bath.

- 4 For example, both ethylene glycol bis(2,3-epoxy-2-methyl-'pro'pyDether and diethylene glycol bis(2,3-epoxy-2- methylpropyDetherhave a solubility in water of greater than 29 percent at 25 C.

Another aspect of the present invention is directed to stabilizedtextile treating solutions containing one or more of the aforesaidpolyepoxides. It has been observed that the polyepoxides tend to undergohydrolysis with water with the net result that the amount of polyepoxidein the treating solution decreases as the hydrolysis reaction proceeds.Due to the acidic nature of many of the catalytic agents employed, thisoccurrence is greatly aggravated where the epoxy curing agent is presentin the treating solution.

In practice, it has been found that a textile treating solutioncontaining from about 1.0 to about 20 percent by weight of polyepoxideand higher, and from about 0.01 to about 10 percent by weight ofsolution of an epoxy curing catalyst may be conveniently stabilizedagainst hydrolysis by the addition of a stabilizing amount of one ormore of the compounds hereinafter mentioned. Although the need forstabilizing the textile treating solutions will largely be determined bythe ingredients present and the particular plant operating procedures,it has been found desirable to stabilize solutions wherein thehydrolysis of the polyepoxide exceeds 10 percent in 8 hours at 30 C.

The buffering agents or stabilizers of the present invention. can be anycompound which will maintain the hydrogen ion concentration of thetextile treating solution at a pH value within the range of from about5.5 to about 7.5 and thereby stabilize the polyepoxide from hydrolysis.Certain precautions must be taken in the choice of bufiering agents inthat they should be substantially unreactive with the epoxy curingcatalyst, the polyepoxide, or other components present in the solution.In practice it has been found that good wash-and-wear properties areimparted to textile materials when they are impregnated with textiletreating solutions which contain one or more bufiering agents which aremembers selected from the class consisting of ammonium hydroxide and theoxides, hydroxides, and salts of the metals designated as group II ofthe periodic classification of the elements, F. Daniels,

' Outline of Physical Chemistry, John Wiley and Sons,

New York, 1952, page 665. Preferred compounds suitable for use in thepractice of this invention are those compounds which are membersselected from the class consisting of ammonium hydroxide and the oxides,hydroxides, carbonates, and lower organic acid salts of magnesium,calcium, strontium, barium, zinc and cadmium. Particularly preferredcompounds which can be employed as stabilizers in the instant inventioninclude, among others, calcium oxide, calcium hydroxide, calciumcarbonate, calcium acetate, barium oxide, barium hydroxide, bariumcarbonate, barium acetate, zinc oxide, zinc hydroxide, zinc carbonate,zinc acetate, cadmium oxide, cadmium hydroxide, cadmium carbonate,cadmium acetate, and the like. a

The amount of stabilizer or buffering agent which can be added is notnecessarily critical and all that is needed is a stabilizing amountsufficient to stabilize the polyepoxide from hydrolysis. This amountwill vary from about 0.01 percent to about 5 percent by weight oftextile treating solution or higher. Preferably, however, from about 0.1percent to about 2 percent by weight is sufiicient. Concentrations aboveand below these amounts can equally as well be employed but are lesspreferred. It has been observed that an aqueous solution containing 15percent by weight of solution of the methylglycidyl ethers end 1.5percent by weight of zinc fluoborate may be conveniently stabilized at25 C. by the addition of approrimately 0.4 percent by weight ofthesolution of zinc 0x1 e.

In still another aspect of the present invention, the stabilized textiletreating solutions can include mixtures of one of more polyepoxides andone or more known textile finishes, particularly the nitrogen-containingfinishes, either alone or in the presence of an epoxy curing catalyst.The undesirable yellowing efiect of the nitrogenous textfle resins afterchlorine bleaching when such resins are used as the sole finish forwhite goods,is eliminated or greatly reduced when employed inconjunction with polyepoxides. Additionally, the combined finishes havea synergistic effect with enhanced wash-and-wear properties. Thus,excellent results are obtained, for example, by the use of themethylglycidyl ethers in conjunction with the melamine-formaldehyderesins, 1,3-dimethylol-5-ethyltetra-hydro-5-triazin-2(1H)-one; monoanddimethylol ureas, monoand dimethylol ethylene ureas, methylated methylolureas, and the like.

The textile treating solutions employed for imparting the wash-and-wearcharacteristics to the cellulosic or cellulosic-containing materials canalso contain, in addition to the aforementioned polyepoxides andnitrogenous textile resins, plasticizers, natural resins, textilesoftening agents and the like.

While the curing step can be accomplished by heating, it can beaccelerated by the use of a suitable epoxy curing catalyst. A variety ofcatalysts are useful in the process of this invention with the borontrifluoride complexes being preferred. Other acids, acidic salts, andLewis acids are also suitable for this purpose. Examples of epoxy curingcatalysts are the fluoborates of magnesium, tin, cadmium and sodium aswell as zinc; boron trifluoride etherate, stannic chloride, boric acid,the alkane sulfonic acids, aluminum chloride, hydrochloric acid,phosphoric acid, oxflic acid, magnesium chloride, sodium sulfate, zincsulfate, aluminum sulfate, and the like. The amount of catalyst employedis not necessarily critical and can vary in amount from about 0.01percent to about percent by weight, with a preferred range of from about0.1 percent to about 5 percent.

The amount of polyepoxide to be applied to the textile material is anamount sufiicient to give a desired washand-wear rating of 4 or 5 ashereinafter indicated. A preferred method is to immerse the fabric in anaqueous solution containing from about 1 to about 30 percent by weightof the epoxy, preferably 3 to 20 percent, and from 0.01 to 10 percent ofthe epoxide curing catalyst and then pass it through a squeeze roller. Asecond immersion and squeezing can be efiected if necessary, leaving thefabric impregnated with approximately 60-120 percent of its own weightof solution. After this padding procedure, the fabric is mounted on apin frame and dried at relatively low temperatures to remove water.While drying may be accomplished by allowing the fabric to remain incontact with the air, a temperature range of from about 35 C. to about80 C. for 5 to 1 minutes is preferred. Since the drying time is notcritical, a wider range of drying temperature can be employed equally aswell.

Upon drying, the fabric is cured at a temperature sufiicient to promotethe reaction of the polyepoxide with the fibrous material being treated.Temperatures from about 200 C. to about 120 C. and more preferably 160C. to 120 C. can be employed for periods ranging from about seconds toabout 15 minutes, with the higher temperatures using the shorter curingperiod. Although the methylglycidyl ethers can be cured over the broadtemperature range noted above, they are particularly unique in that theycan be cured at low temperatures with consequently less damaging effecton the fabric.

After the curing step, the fabric is scoured to remove unreactedpolyepoxide or epoxy curing catalyst. Scouring is effected by washing inhot water (5080 C.) containing a small quantity of detergent. Thescouring conditions themselves are not critical as long as unreactedmaterial is removed from the fabric. After scouring, the fabric is driedand evaluated.

The cellulosic textile fabrics used to illustrate the process of thisinvention were x 80 cotton print cloth and 80 x 80 staple rayon fabric.The fabric was white, had been scoured and bleached, and was in suitablecondition for application of resin treatment.

In the evaluation of the properties of the treated fabric, the followingtests were conducted:

(a) Breaking strength; measured by the raveled strip method (AmericanSociety for Testing Materials D39- 49).

(b) Crease recovery; measured with the Monsanto tester (American Societyfor Testing Materials D1295- 531). By this test the ability of a fabricto recover from a crushing fold is measured.

(0) Dimensional stability; American Association of Textile Chemists andColorists, tentative test method 40- 52.

(d) Wash and Wear evaluation; by means of the following scale, thewash-and-wear" properties of the treated material were evaluated.

Scale: Evaluation 5 As ironed.

4 Wearable. 3 Needs ironing. 2 Not acceptable. 1 Very wrinkled.

Ref: Textile Research Journal, 26, 974 (1956) American DyestufiReporter, 43, 37 (1959).

(2) Color; the yellowness of the treated fabric was determined bycomparison with the original bleached fabric. The yellowness index wasdetermined using a Hunter multi-purpose refiectometer. This abridgedspectrophotometer employs three filters in measuring the 45, 0reflectance of a fabric with respect to amber, green and blue light. Asimple yellowness index is provided by Yellowness= Example I A treatingsolution was prepared which contained 20 percent by weight of diethyleneglycol bis(2,3epoxy-2- methylpropyl)ether and 0.5 percent by weight ofzinc fluoborate, the remainder being water. A sample of 80 x 80 cottonprint cloth was immersed in this solution, padded to a wet pick-up of 98percent of the fabric weight and dried for five minutes at 40 C. Thefabric was cured for 3 minutes at C. and then laundered with a 0.1percent solution of a built anionic detergent to remove residualreagents. After drying and conditioning to 65 percent relative humidity,the dry add-on was found to be 14.3 percent. The crease recovery of thetreated sample was 78 percent, the breaking strength retained was 66percent of the original fabric, and the sample had a wash-and-wear indexof 3.

The original untreated fabric was immersed in water, dried and found tohave a crease recovery of only 44 percent.

Example I] A sample of 80 x 80 cotton print cloth was treated in amanner similar to that described in Example 1, except that theconcentration of zinc fiuoborate catalyst was 1.0 percent by weight ofthe treating solution and the fabric was cured for 3 mintues-at 160 C.The treated fabric had a dry add-on of 14.3 percent, a crease recoveryof 79 percent, a' breaking strength retention of 64 percent and awash-and-wear index of 4.

Example III A sample of 80 x 80 cotton print cloth was treated in amanner similar to that described in Example 11, except that theconcentration of zinc fiuoborate catalyst was 4.0 percent by weight ofthe treating solution. The treated sample had a dry add-onof 12.0percent, a crease recovery of 75 percent, a breaking strength retentionof 63 pereentand a wash-and-wear index of 4.

Example IV A sample of 80 x 80 cotton print cloth was immersed in atreating solution which contained 20 percent by Weight of'ethyleneglycol bis(2,3-epoxy-2-methylpropyl)- ether and 1.6 percent by weight ofzinc fluoborate, the remainder being water. The sample was dried forminutes at 38 C., cured for 2 minutes at 191 C., and laundered to removeresidual reactants. The treated fabric had a dry add-on of 7.4 percent,a crease recovery of 52 percent, a breaking strength retention of 67percent, and a wash-and-Wear index of '3.

Example V A sample 80 x 80 cotton print cloth was immersed in a treatingsolution which contained 21.5 percent by weight of ethylene glycolbis(2,3-epoxy2-methylpropyl)ether, 1.4 percent by weight of zincfiuoborate, and 0.4 percent of zinc oxide, the remainder being water.The sample was padded to a wet pick-up of 74 percent of the fabricweight and dried for 2.5 minutes at 77 C. The fabric was cured for 3minutes at 120 C. and then laundered to remove residual reactants. Thetreated sample was found to have a dry add-on of 8.3 percent, a creaserecovery of 71 percent, a breaking strength retention of 60 percent anda wash-and-wear index of 4.

Example VI A sample of 80 x 80 cotton print cloth was treated in amanner similar to that described in Example V, except that the zincoxide buffering agent'was omitted and the solution was allowed to standfor 3 hours prior to padding. The sample waspadded to a wet pick-up of82 percent by weight of the fabric. The sample was found to have a dryadd-on of 8.6 percent, a crease recovery of 61 percent, a breakingstrength retention of 70 percent and a wash-and-wear index of 2.

The stabilizing effect of the zinc oxide buffering agent on thehydrolysis of the polyepoxide is evident from the foregoing data.

Example VII A treating solution was prepared which contained 6.7 percentby weight of ethylene glycol bis(2,3-epoxy-2- methylpropyl)ether, 3.4percent of dimethylol ethylene urea, 0.7 percent of zinc fluoborate, 0.5percent zinc oxide and 88.7 percent water. A sample of 80 x 80 cottonprint cloth was immersed in this solution and padded to a wet pick-up of74 percent of the fabric Weight and dried for 3 minutes at 75 C. Thefabric was cured for 3 minutes at 120 C. and then laundered to removeresidual reactants. After drying the sample was found to have a dryadd-on of 4.3 percent, a crease recovery of 69 percent, a breakingstrength retention of 62 percent and a washand-wear index of 4.

Example Vlll A treating solution was prepared which contained 6.7percent by weight of ethylene glycol bis((2,3-epoxy-2-methy1propyl)ether, 3.4 percent of 1,3-dimethylol-5--ethyl-tetrahydro5-triazin(2H)-one, 1.4 percent of Zinc fluoroborate,0.5 percent zinc oxide and 88 percent Water. A sample of 80 x 80 cottonprint cloth was immersedin this solution and padded to ,a wet pick-up of83 percent of the fabric weight and dried for 3 minutes at C. The fabricwas'cured for 3 minutes at 160 C. and then laundered to remove residualreactants. After drying the sample was found to have a dry add-on of 4.9percent, a crease recovery of '69 percent, a breaking strength retentionof 62 percent and a wash-and-wear index'of 5.

. Example IX A treating solution was prepared which contained 6.7percent by 'weight of ethylene glycol bis(2,3-epox-2-methy1propyl)ether, 3.4 percent of a modified melamineformal dehyderesin produced by American Cyanamid Co. and sold under the name AerotexResin MW, 0.7 percent zinc fluoborate, 0.5 percent Zinc oxide and 88.7percent water. A sample of x 80 cotton print cloth was immersed in thissolution and padded to a wet pickup of 82 percent of the fabric weightand dried for 3 minutes at 75 C. The fabric was cured for 3 minutes atC. and then laundered to remove residual reactants. After drying thesample was found to have a dry add-on of 4.4 percent, a crease recoveryof 67 percent, a breaking strength retention of 65 percent and aWash-and-wear index of 3.

Example X A treating solution was prepared which contained 20 percent byweight of bis(2,3-epoxy-2-methylpropyl)- ether, 1.6 percent by weight ofzinc fiuoborate, 2 percent of poly(vinyl alcohol), the remainder beingwater. A sample of 80 x 80 cotton print cloth was padded to a wetpick-upof 95 percent of the fabric weight and dried for five minutes at 38 C.The fabric was cured for 2 minutes at C. and then laundered with a 0.1percent solution of a built detergent to remove residual reagents. Thetreated fabric had a dry add-on of 8.5 percent, a crease recovery of 66percent, a breaking strength retention of 59 percent and a wash-and-wearindex of 3.

Although the invention has been illustrated by the preceding examples,the invention is not to be construed as limited to the materialsemployed in the above examples, but rather, the invention encompassesthe generic area as hereinbefore disclosed. Various modifications andembodiments of this invention can be made without departing from thespirit and scope thereof.

What is claimed is:

1. A process for treating cellulosic and cellulosic-containing textilematerial whereby said material is rendered both shrink and creaseresistant while imparting to said material after laundering a softsmooth finish without ironing which comprises impregnating said textilematerial with a textile treating solution comprising a monomericpolyepoxide having at least one group, an epoxy curing catalyst and thenheating the textile material to cure the polyepoxide.

2. A process as claimed in claim 1 wherein the textile material iscotton.

3. A process as claimed in claim 1 wherein the textile material israyon.

4. A process as claimed in claim 1 wherein the textile material islinen.

5. A process as claimed in claim 4 wherein the polyepoxide isbis(2,3-epoxy-2-methylpropy1)ether.

6. A process as claimed in claim 4 wherein the polyepoxide is ethyleneglycol bis(2,3-epoxy-2.-rnethylpropyl)- ether.

7. A process as claimed in claim 4 wherein the polyepoxide is diethyleneglycol bis(2,3-epoxy-2-methylpropyl)ether.

8. A process as claimed in claim 6 wherein the epoxide curing catalystis zinc fluoborate.

9. A process as claimed in claim 4 wherein the fabric is heated withinthe temperature range of from about 200 C. to about 120 C. for a periodof from about 15 seconds to about 15 minutes.

10. A process for treating cellulosic and cellulosic-containing textilematerial whereby said material is rendered both shrink and creaseresistant while imparting to said material after laundering, a soft,smooth finish without ironing which comprises impregnating said textilematerial with a textile treating solution comprising a monomericpolyepoxde having at least one CH3 CH7-CH7O- group, an epoxy curingcatalyst, a buffering agent and then heating the textile material tocure the polyepoxide.

11. A process for treating cellulosic and cellulosiccontaining textilematerial whereby said material is rendered both shrink and creaseresistant while imparting to said material after laundering, a soft,smooth finish without ironing which comprises impregnating said textilematerial with a textile treating solution comprising a monomericpolyepoxide having at least one group, and from about 0.01 to about 10percent by weight of an epoxy curing catalyst and heating the textilematerial to cure the polyepoxide.

References Cited in the file of this patent UNITED STATES PATENTS Condoet al June 26, 1956 Thomas Apr. 1, 1958

1. A PROCESS FOR TREATING CELLULOSIC AND CELLULOSIC-CONTAINING TEXTILEMATERIAL WHEREBY SAID MATERIAL IS RENDERED BOTH SHRINK AND CREASERESISTANT WHILE IMPARTING TO SAID MATERIAL AFTER LAUNDERING A SOFTSMOOTH FINISH WITHOUT IRONING WHICH COMPRISES IMPREGNATING SAID TEXTILEMATERIAL WITH A TEXTILE TREATING SOLUTION COMPRISING A MONOMERICPOLYEPOXIDE HAVING AT LEAST ONE